Mike Tyson Reflects on Career & Struggles Before Jake Paul Fight

Mike Tyson reflects on the highs and lows of his tumultuous life and boxing career, acknowledging the personal costs of his success and preparing for a comeback fight against Jake Paul on November 15.


Mike Tyson’s journey in boxing has been nothing short of legendary, filled with both triumph and turmoil. But he wants everyone to know there’s a hefty price tag attached to his success.

His life story, often blurring the lines between fact and myth, has been dissected through countless words and footage. On Nov. 15, Tyson, now 58, adds another chapter by stepping back into the ring after 19 years to face influencer boxer Jake Paul at AT&T Stadium in Arlington, Texas.

Before this much-anticipated match, Tyson sat down with Andre Ward on The Art of Ward podcast. Reflecting on becoming the youngest heavyweight champ at just 20, his response was surprisingly brief.

“I don’t wish that on no one,” Tyson confessed. “My life as a whole? I don’t wish it on anyone.”

He elaborated further: “I wanted it all. To be the biggest fighter ever—that’s what Cus D’Amato instilled in me. It was like he programmed those words into my mind.”

Tyson skyrocketed to fame after defeating Trevor Berbick in 1986 for the WBC heavyweight title. His knockouts became legendary, notably needing just over 90 seconds to take down Michael Spinks two years later.

However, a dramatic fall from grace ensued. A shocking loss to Buster Douglas in 1990 was followed by a 1992 rape conviction, leading to three years behind bars. Tragedy struck again in 2009 when his four-year-old daughter passed away in an accident.

Despite personal struggles—many self-inflicted—Tyson has slowly reclaimed respect as a combat sports elder statesman over the past 15 years. He recalls his initial comeback in 1995 post-prison as less successful than it seemed.

“I was still trapped,” Tyson admitted. “Lost everything—money, sobriety. Went through AA and sex addiction programs. Starting over with nothing but experience changed my financial and personal life completely.”

“I was escaping,” he continued. “Shame, embarrassment… wanting to die even. But something inside kept pushing me forward. Tried movies, Broadway—but nothing compares to fighting. I’d fight for free over Hollywood any day.”

After losing to Douglas, Tyson felt supported but realizes now it was only because his fame hadn’t faded yet.

“Not really,” Tyson said about having support. “Once your money’s gone, so are they.”

“Enemies can’t hurt you,” he mused. “Only friends can… We’re all preparing for an expiration date. When we truly live, that’s when it’s time to go.”

Catch Tyson vs. Paul live on Netflix this Nov. 15.

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